322
Views
8
CrossRef citations to date
0
Altmetric
Articles

Asymmetric flavone-based liquid crystals: synthesis and properties

, , , , , & show all
Pages 1436-1449 | Received 06 Sep 2016, Accepted 09 Jan 2017, Published online: 01 Feb 2017

References

  • Da Rosa RR, Tariq M, Weber CS, et al. Hybrid liquid crystals tetrazolyl and isoxazolyl cinnamates. Liq Cryst. 2016;43:1659–1670.
  • Elgueta EY, Parra ML, Barberá J, et al. New polycatenar schiff bases derived from 1,3,4-thiadiazole: synthesis, mesomorphism and luminescence behaviour. Liq Cryst. 2016;43:1649–1658.
  • Gallardo H, Santos DMDO, Caramori GF, et al. Synthetic pathway for a new series of liquid crystal 2,6-disubstituted imidazo[2,1-b][1,3,4]thiadiazole. Liq Cryst. 2013;40:570–580.
  • Chia WL, Lin CW. Synthesis and thermotropic studies of a novel series of nematogenic liquid crystals 2-(6-alkoxynaphthalen-2-yl)-5-cyanopyridines. Liq Cryst. 2013;40:922–931.
  • Benbayer C, Saïdi-Besbes S, Grelet E, et al. Structure-property study of new [1,2,3]-triazole liquid crystalline derivates. Liq Cryst. 2013;40:1520–1528.
  • Van Acker FA, Hageman JA, Haenen GM, et al. Synthesis of novel 3,7-substituted-2-(3ʹ,4ʹ-dihydroxyphenyl)flavones with improved antioxidant activity. J Med Chem. 2000;43:3752–3760.
  • Zapata-Torres G, Opazo F, Salgado C, et al. Effects of natural flavones and flavonols on the kinase activity of Cdk5. J Nat Prod. 2004;67:416–420.
  • Verma AK, Singh H, Satyanarayana M, et al. Flavone-based novel antidiabetic and antidyslipidemic agents. J Med Chem. 2012;55:4551–4567.
  • Kim Y, Hackett JC, Brueggemeir RW. Synthesis and aromatase inhibitory activity of novel pyridine-containing isoflavones. J Med Chem. 2004;47:4032–4040.
  • Yao N, Chen C, Wu C, et al. Novel flavonoids with antiproliferative activities against breast cancer cells. J Med Chem. 2011;54:4339–4349.
  • Zhang J, Lv Y, Zhang W, et al. A flavone-based turn-on fluorescent probe for intracellular cysteine/homocysteine sensing with high selectivity. Talanta. 2016;146:41–48.
  • Liu B, Wang J, Zhang G, et al. Flavone-based ESIPT ratiometric chemodosimeter for detection of cysteine in living cells. ACS Appl Mater Interfaces. 2014;6:4402–4407.
  • Yeap G, Yam W, Takeuchi D, et al. Synthesis, thermal stabilities, and anisotropic properties of some new isoflavone-based ester 7-decanoyloxy-3-(4ʹ-substitutedphenyl)-4H-1-benzopyran-4-ones. Liq Cryst. 2008;35:315–323.
  • Yeap G, Yam W, Takeuchi D, et al. Synthesis and phase behavior of new isoflavone derivatives: crystal structure of 7-hexyloxy-3-[4ʹ-(3-methylbutyloxy)phenyl]-4H-1-benzopyran-4-one. Mol Cryst Liq Cryst. 2008;482:87–102.
  • Yeap G, Yam W, Ito MM, et al. Synthesis and phase behavior of some isoflavone derivatives. Ferroelectrics. 2008;365:65–77.
  • Belmar J, Parra M, Zuniga C, et al. Synthesis of new mesogenic compounds having the isoflavone core group. Liq Cryst. 1999;26:75–81.
  • Yuvaraj AR, Yam WS, Chan TN, et al. New para-substituted non-symmetric isoflavones for their fast photo-switching ability: synthesis and their liquid crystal characterization. Spectrochim Acta A. 2015;135:1115–1122.
  • Chan TN, Lu Z, Yam WS, et al. Non-symmetric liquid crystal dimers containing an isoflavones moiety. Liq Cryst. 2012;39:393–402.
  • Yeap GY, Chan TN, Yam WS, et al. Non-symmetric chiral isoflavones dimers: synthesis, characterisation and mesomorphic behaviour. Liq Cryst. 2012;39:1041–1047.
  • Hirose T, Tsuya K, Nishigaki T, et al. Phase transitions of 6-(4-n-alkyloxybenzoyloxy)-flavones and 3-cyano-7-(4-n-alkyloxybenoyloxy)-coumarins. Liq Cryst. 1989;4:653–659.
  • Frish MJ, Trucks GW, Schlegel HB, et al. Gaussian 09, Revision E.01. Wallingford CT: Gaussian, Inc.; 2009.
  • Dennington R, Keith T, Millam J. Gaussview, version 5. Shawnee Mission, KS: Semichem Inc.; 2009.
  • DFT (B3LYP) calculations were performed using a 3-21G basis set for 4ʹ-decyloxy-6-methoxyflavone and 4ʹ-decyloxy-7-methoxyisoflavone. The dipole moments were 5.1126 D and 3.0844 D, respectively. See Supplementary Materials for details
  • Sagrera G, Seoane G. Total synthesis of 3ʹ,3ʹʺ-binaringenin and related bioflavonoids. Synthesis. 2010;2010:2776–2786.
  • Lee TH, Chen JT, Hsu CS. Synthesis of cyclopentyloxy terphenyl liquid crystals with negative dielectric anisotropy. Liq Cryst. 2015;42:104–112.
  • Hendrickson HP, Kaufman AD, Lunte CE. Electrochemistry of catechol-containing flavonoids. J Pharm Biomed Anal. 1994;12:325–334.
  • Hendrickson HP, Sahafayen M, Bell MA, et al. Relationship of flavonoid oxidation potential and effect on rat hepatic microsomal metabolism of benzene and phenol. J Pharm Biomed Anal. 1994;12:335–341.
  • Hodnick WF, Milosavljević EB, Nelson JH, et al. Electrochemistry of flavonoids. Biochem Pharma. 1988;37:2607–2611.
  • Medvidović-Kosanović M, Šeruga M, Jakobek L, et al. Electrochemical and antioxidant properties of (+)-catechin, quercetin and rutin. Croat Chem Acta. 2010;83:197–207.
  • Arroyo-Currás N, Videa MF. Electrochemical study of flavonoids in acetonitrile: structure-activity relationships. ECS Trans. 2010;29:349–359.
  • Wolfbeis OS, Begum M, Geiger H. Fluorescence properties of hydroxyl- and methoxyflavones and the effect of shift reagents. Z. Naturforsch. 1984;39b:231–237.
  • CrysAlisPro Software System. v1.171.35.1, Rigaku Oxford Diffraction. Oxford, UK: Rigaku Corporation; 2015.
  • Sheldrick GM. A short history of SHELX. Acta Cryst. 2008;A64:112–122.
  • Dolomanov OV, Bourhis LJ, Gildea RJ, et al. J Appl Cryst. 2009;42:339–341.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.